Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Patent
1995-06-26
1996-08-20
Krass, Frederick
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
525420, 528328, 528363, 562553, 4273884, 134 2, 134 4, 134 7, 134 13, 527314, C86G 6908, C86G 6910, C86G 7310, C86G 7306
Patent
active
055480365
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for preparing polymers of aspartic acid by thermal condensation of monoamides of maleic acid, fumaric acid or the ammonium salts of the monoamides of these acids, in the presence or absence of compounds capable of cocondensation, and to the use of the polymers as scale inhibitors, as dispersants for pigments and as additive to detergents and cleaners.
Polyaspartic acid and condensates of aspartic acid with other amino acids are known.
Thus, for example, Nature 163 (1949) 213 describes the formation of high molecular weight condensation products on heating aspartic acid at 200.degree. C. J. Amer. Chem. Soc. 74(1952) 5304 and 5307 disclose the thermal polycondensation of aspartic acid/glutamic acid mixtures in the presence of phosphoric acid.
Arch. Biochem. Biophys. 86 (1960) 281-285 describes the polycondensation of amino acid mixtures composed of 2 parts of glutamic acid, 2 parts of aspartic acid and one part of a mixture of other amino acids in the presence of phosphoric acid at over 100.degree. C. Proteinoids are obtained in increasing yields and with higher molecular weights as the condensation temperature increases. The proteinoids contain 10-30 mol-% glutamic acid units. The glutamic acid units are mainly located at the chain ends. The molecular weights may reach 35000.
According to the Journal of the Americal Chemical Society 80 (1958) 2694, purely thermal treatment of glutamic acid results almost quantitatively in pyroglutamic acid which is incapable of polycondensation.-However, polycondensates which contain glutamic acid units can be prepared by copolycondensation of glutamic acid and other amino acids.
Nature 190 (1961) 531 and Polym. Bull. 1 (1978) 177-180 describe the thermal polycondensation of L-asparagine and isoasparagine in boiling water to form polyaspartic acids with average molecular weights of up to 3000.
J. Org. Chem. 26 (1961) 1084 describes the polycondensation of N-acetylaspartic acid at 145.degree.-200.degree. C. with elimination of water and acetic acid to form a glassy solid which has been identified as polyaspartimide. This reference also describes the polycondensation of the hydrobromide of aspartic anhydride in pyridine.
A method using phosphoric acid for the polycondensation of DL-aspartic acid is described by Neri in J. Med. Chem. 16 (1972) 893-897. At a phosphoric acid/aspartic acid molar ratio of 0.6 the resulting polyaspartimide has, as a solution in dimethylformamide, a reduced viscosity of 45 ml/g. Subsequent reaction with ethanolamide results in a modified polyaspartic acid which is suitable as plasma expander. The reaction is carried out in dimethylformamide as solvent.
EP-B--0 256 366 discloses a process for preparing polyaspartic acid and its salts in which maleic acid and ammonia are reacted in the molar ratio 1: 1-1.5 at from 125 to 140.degree. C., and the acids are, where appropriate, converted into their salts. It is also possible to use maleic anhydride in the reaction, maleic acid being initially prepared therefrom by addition of water. U.S. Pat. No. 5,057,597 discloses the polycondensation of aspartic acid crystals in an agitated fluidized bed.
It is an object of the present invention to provide a process which can easily be carried out industrially to prepare polymers of aspartic acid.
We have found that this object is achieved by a process for preparing polymers of aspartic acid by thermal condensation of monoamides of maleic acid, fumaric acid or the ammonium salts of the monoamides of these acids, in the presence or absence of compounds capable of cocondensation, wherein give monoamides of maleic acid, fumaric acid or their ammonium salts at up to 100.degree. C., the reaction products are subsequently thermally condensed, with or without compounds capable of cocondensation, at above 100.degree. C., and the condensates are hydrolyzed where appropriate. The reaction of maleic anhydride and ammonia and/or primary or secondary amines is preferably carried out below the melting point of the maleic anhydride or the mi
REFERENCES:
patent: 5284512 (1994-02-01), Koskan et al.
patent: 5373088 (1994-12-01), Koskan et al.
patent: 5399750 (1995-03-01), Brun et al.
Derwent Abstracts 73-49652U, "Maleic Acid Monoamide Preparation".
Journal of Medicinal Chemistry, vol. 16, pp. 893-897, (1973).
Archives of Biochemistry and Biophysics, vol. 86, 280-285, (1960).
The Journal of Organic Chemistry, vol. 26, pp. 1084-1091, (Jan.-Apr. 1961).
The Journal of the American Chemical Society, vol. 74, pp. 5304-5306, (Oct. -Dec. 1952).
Polymer Bulletin, vol. 1, pp. 177-180, (1978-1979).
Nature, vol. 163, pp. 213, 214 (1949).
Nature, vol.190, pp. 531-532, (Apr. 1, 1961 to Jun. 24, 1961).
Journal of the American Chemical Society, vol. 80, pp. 1523-2697, (Apr. 11, 1958).
Baur Richard
Hartmann Heinrich
Kroner Matthias
Kud Alexander
Potthoff-Karl Birgit
BASF - Aktiengesellschaft
Krass Frederick
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